Vacation rentals with a kayak in Philipstown

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Top-rated kayak rentals in Philipstown

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Guest favorite

Home in New Paltz

4.94 out of 5 average rating, 173 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Perched on the water’s edge, you’ll look down from this bright, modern post at an expanse of winding river and broad tree-lined meadows. Let the mellow current and enveloping natural setting satisfy and soothe your senses. This special place is close to everything, making it an ideal launchpad to all the Hudson Valley has to offer. Kingston, New Paltz and Rosendale are all ten minutes away, surrounding you with a plethora of hiking trails, climbing, dining, drinking, entertainment and shopping.

Jan 5 – 12

ﺩ.ﺇ1,197 per night

Guest favorite

Cottage in Highland Lakes

4.97 out of 5 average rating, 269 reviews

The Mountaintop Lakehouse that Time Forgot.

Quiet Private lakehouse set down on 2 rare rock bluffs giving you a majestic water view just like it was in 1939. Extra Lg Great room w a huge fireplace. The great kitchen surrounds the chef. Big hot tub, Rowboat with canopy, 8 kayaks, Treehouse, Neverending Lakeside windows, docks, 1 hr from Manhattan w Eagles & vast wildlife like you were in the deep woods. Clean, unspoiled lake full of fish. Never had gas motors. A Mountaintop lake above the ski area. Stargazing! Perfect for get-togethers.

Mar 19 – 26

ﺩ.ﺇ1,450 per night

Superhost

Cottage in Putnam Valley

4.89 out of 5 average rating, 216 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Oct 10 – 17

ﺩ.ﺇ1,430 per night

Guest favorite

Cabin in Huguenot

4.95 out of 5 average rating, 238 reviews

Tranquil Lakefront Cabin!

This Warm LAKEFRONT Home Grabs Your Soul and Forces you to Decompress Instantly. Enjoy the Large Well Appointed Screened Porch with Glass of Wine/Cup of Coffee as you Gaze over the Rustic Lake thru Stately Oak Trees and Cranberry Bogs. Boats Included!!! $50 Per Pet Per Stay… http://wpdh.com/airbnb-announces-hudson-valley-as-top-destination-in-the-world/?fbclid=IwAR32OGbKzPHj2WtVhQmXslZ9xZo9dNVnmp1nTL9mF_xOSaAFMDTnkhRsDA8 FOLLOW US ON INSTAGRAM https://instagram.com/tranquil_lakefront

Sep 23 – 30

ﺩ.ﺇ548 per night

Guest favorite

Home in Putnam Valley

4.96 out of 5 average rating, 102 reviews

Lake Cottage Near Sleepy Hollow, Westpoint & NYC

Escape to this private lakeside cottage. Just 1h drive from NYC near lots of skiing: Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away The cottage can accommodate up to 10 guests and is family-friendly. Pets are welcome! WiFi is extremely fast and we have free electric car charging.

Jul 29 – Aug 5

ﺩ.ﺇ2,673 per night

Guest favorite

Cottage in Monroe

5.0 out of 5 average rating, 129 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Jul 6 – 13

ﺩ.ﺇ2,226 per night

Guest favorite

Home in Greenwood Lake

4.95 out of 5 average rating, 195 reviews

Stylish Lakeside Chalet with Hot Tub

Welcome to Greenwood Lakeside Chalet, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

Sep 19 – 26

ﺩ.ﺇ1,403 per night

Guest favorite

Cabin in West Milford

4.98 out of 5 average rating, 113 reviews

Peaceful Lake Front Log Cabin w/3 bedrooms up to 7

Enjoy this peaceful lake front log cabin all to yourself and 6 more of family or friends! Sleeps 7. We are located just an hour from NYC. The cabin has recently been refinished with a new kitchen, appliances and all new furniture. Relax in our Lake front yard where you'll find a seating area with a firepit, large table for all your sunset dinners, a 2 person Hammock and a large BBQ. The cabin's location to many seasonal activities and events makes this an ideal year round destination!

Jan 23 – 30

ﺩ.ﺇ1,433 per night

Guest favorite

Guesthouse in Gardiner

4.99 out of 5 average rating, 137 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

Our one-bedroom guest house offers serenity and privacy on the Shawangunk Kill river, surrounded by the natural beauty of local farmland and "the Gunks" mountains. Step outside to soak in the tub, kayak, enjoy a bbq, or gather around the firepit. When the spirit of exploration calls you, it's only a short drive to hiking, biking, and world-class rock climbing, along with wineries, breweries, farms, orchards, cider mills, and many fine restaurants. A retreat for body, mind, and soul.

May 28 – Jun 4

ﺩ.ﺇ767 per night

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 312 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Feb 18 – 25

ﺩ.ﺇ1,647 per night

Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 258 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars. Find us on IG @thelittlecabins

Apr 13 – 20

ﺩ.ﺇ1,136 per night

Superhost

Cottage in Phoenicia

4.91 out of 5 average rating, 578 reviews

Romantic Getaway: Lovingly Restored Esopus Cottage

This cottage is perfect for relaxation, working remotely and as a hub for experiencing the majestic Catskills. Featured in Curbed NY, a travel magazine, as “The Best Vacation Rentals in the Hudson Valley," the Esopus Cottage has over 1500 five-star reviews. As Superhosts for 10+ years, we are committed to stellar customer service and making your vacation a memorable and restorative experience. License # 2023-STR-055P

Jul 20 – 27

ﺩ.ﺇ527 per night